Chemistry of N-chloronortropine derivatives: Synthesis of a bridged aziridine compound and new tropane derivatives

An unsymmetrical bridged aziridine compound was obtained from N-chloronortropinone. This compound was found to react with acyl halides, acid anhydrides, and other reagents, including a Michael acceptor, dimethyl acetylenedicarboxylate (DMAD), giving new tropane bases with a ketone functional group at the bridged ethylene moiety. In the case of Michael-type addition, the retention of the aziridine ring system was observed in some solvents.